This week, a 32-year-old living at his parents’ house while navigating a career change: bisexual, corporate job, Pennsylvania.
9 a.m. I’m feeling a bit fuzzy, like “this isn’t a hangover, but I can tell I drank last night.” It’s something I say when I don’t want to admit I’m hungover.
I’m away for the weekend, and went barhopping with my college best friend last night. He’s not waking up anytime soon, which suits me, because I’ve got smutty plans. I have a cup of tea and some toast on the back deck with his wife, and text Ryan to see if those plans are still in play.
Ryan is a FWB I met years ago when living in this area. He was married, experienced, and hot. I was inexperienced and in the closet. I messed around semi-frequently with him and his husband, and we’ve remained in touch — he’s kind of been my gay sex Yoda, someone I’ve felt comfortable asking those questions you didn’t know who else to ask (Example: how does one douche?). I usually stop by and have some fun with them when I’m back in the area, and as luck will have it, plans are still on.
10:30 a.m. I arrive at Ryan and his husband Kevin’s house and we pretend to care about polite niceties for approximately 60 seconds before the three of us head upstairs. Both of them are tall and thin, with worked-out, but not overly ripped bodies. Both are excellent kissers. We take turns kissing and going down on one another, before Kevin asks if I’m ready to take it. I am.
I’ve only been bottoming for about a year now. I’d always been curious … and scared … and for some of those closeted years thought taking it up the ass would somehow make me gayer than, I don’t know, sucking a dick? I hardly think I’m the first guy to think that way, but it’s still kind of embarrassing. I don’t know that I’d say it’s my natural calling, but I enjoy it with the right guy, if it’s someone I know and trust … and mostly if I’m bottoming, I’m on top.
I’m not on top here, and Kevin’s not gentle. He has sex with me from behind until Ryan takes over. His dick is much bigger, but his stamina is not, which is not a dig. I don’t think I could’ve taken any more. My whole body feels tingly.
11:30 a.m. I used to hook up with these guys, and then quickly run out of the house. Now, I shower, have a drink, and catch up. I’m going to be sore tomorrow, but I’ll be damned if I don’t feel like a million bucks, lightheaded in the best way.
2 p.m. Time for an afternoon hang with Matt, a guy I’ve seen three times before when I’m down in this part of the state. We met on Grindr, and obviously we’re going to be naked, but we also talk a lot before and after the naked stuff. I haven’t been out a full year, so I don’t think I’m ready to settle down with anyone just yet, but if I were, he’d be a contender. He’s also a lot of fun, we have a ton of mutual interests, and he has that dark sense of humor I dig. He did tell me before we met that he had an eight-inch dick. He doesn’t. I don’t get why guys do that. If anyone asks, I tell them mine’s average, because you know what? It is. Why advertise what’s not there?
6 p.m. We had a really fun day at a local brewery and have retired to his place.
He’s a great kisser, and even though I wasn’t planning on it, I get on and ride him. It’s our first time having penetrative sex. His face when I make him climax is both devastatingly handsome and cute at the same time. I’m not necessarily proud of the fact that I’ve had three dicks in me today, but ya know what? YOLO, as the kids say.
4 a.m. Since I didn’t come last night (I usually don’t when bottoming), Matt wakes me up with a blow job. He’s not great at it, but I forgive him because he looks great down there.
6 a.m. I manage to ride him again when we wake up the second time, and I come! I’m still revved up from yesterday. He can’t come that way so we switch to doggy. That does the trick. I duck-walk to the car for the drive home.
7:30 a.m. I hate that I’m on Grindr at the rest stop. Like again, three dicks in me yesterday. I think it’s more out of boredom than anything, but still. A blank profile messages me from 28 feet away. “Thank you for being so sexy,” he says. I recently put my face on Grindr and am regretting it. “Can I suck your dick in the bathroom? I’m hard watching you.” I mean, I get not showing your face. I did it that way for years, so I’m not going to judge him for that. But I am going to judge him for coming at me like a goddamn serial killer.
4:30 p.m. I work in a call center. It’s not ideal, but I’ve been trying to do a career switch and it’s not going as planned. So for now, this is paying the bills. Today my younger co-workers are teaching me about this Eminem feud. I learn what a Machine Gun Kelly is, and I think I’m dumber for it. I’ve reached that point where I don’t care to learn what the kids are listening to these days.
7 p.m. I just started watching the final season of The Americans. I don’t know who I’m more into, Matthew Rhys or Keri Russell? I’m going with Keri. I would let Elizabeth Jennings have her way with me.
5 a.m. I actually go through with an early gym session. Nice! I do push-ups, burpees, and jump rope. It feels good to get it out of the way this early. I hit the sauna afterward. Nothing sexy is going to happen here. Although I personally know people who’ve hooked up in the gym, I still sort of think it’s an urban legend. Also, I worked at a gym in high school. I had to clean the sauna. I know that life and I’m not about to let some poor guy making minimum wage clean up evaporated cum.
12 p.m. I don’t have to go in to work until two today, which is why I’m killing time at a coffee shop. What do I do? Log onto Grindr because I can’t help myself. This really hot, ripped guy from Chicago messages me. He’s just here on a layover. Did I mention he’s really hot and I’m weak of mind and spirit?
1 p.m. Too often these quick Grindr encounters end with orgasms and immediate shame (shout-out to Catholic education!). This one didn’t. He was a great kisser, which is big for me, and even hotter in person. We made out and traded oral.
7 p.m. Work was work. For the past two months, I was in the interview process for a position I really wanted, but I learned last week they went with another candidate. When I asked for feedback, they told me to keep striving for my goals and requested I follow them on Instagram …
8:30 p.m. I have a date with a guy I met on Tinder. I’m exhausted as all hell, and kind of want to bail, but am obsessed with being polite.
9:30 p.m. Now I wish I’d bailed. He fancied himself an intellectual elitist (name checked The New Yorker too many times, pronounced Barcelona “Barthelona”), but didn’t have the charm to pull it off. I like highbrow/lowbrow guys — be able to talk NPR and Jersey Shore. Just when I think I’m being too judgmental, he starts telling me how Stormy Daniels’s lawyer should be our next president. Check, please.
10:45 p.m. Bed. Attempt to watch Wild Wild Country due to recommendations. Not into it. Watch some porn instead. Do I subscribe to Seth Fornea’s OnlyFans account? Yes. Am I proud of that? No. Is it worth it? Yes.
5 a.m. Another successful workout! I take a gym-douche selfie in the locker room and send it to Matt. He replies with him naked, a towel hanging from his hard dick. SWOON.
8:30 a.m. I get some unexpected good news: Chad, a guy I hooked up with over the summer, is going to be in town on business tonight and wants to know if I want to get together. He and his boyfriend were here this summer, and I fucked him while his boyfriend watched. It was insanely hot. They turned out to be cool guys too, which was sweet. He’s alone tonight. I’m in.
12:30 p.m. Chad and I have been texting all day. I’m so pent up. I legitimately consider jerking off in the office bathroom.
9:30 p.m. Leaving the Marriott after three hours of sex with Chad, sweaty, exhausted, and probably glowing. I fucked him three times in three hours, which honestly, I didn’t think I had in me. The first time we did it over FaceTime for his bf. The second was in the shower afterward. The third was on the bed after that. My sex life is hot and cold, and very rarely consistent. I probably won’t get laid now for at least three months.
10:30 p.m. Have a nice talk with my mom. Yes, the whole career transition has me back with my folks to save some cash. It’s not ideal, and I feel weird talking with my mom over milk and Oreos right after a three-hour fuck-fest, but in general I really like my parents, and think I’ll look back on this time with fondness.
She told me how my dad told her that someone said “fag” around him at work today, and he told them to quit it. The co-worker asked why, and he said because my son is gay and I won’t tolerate that. If I’m being honest, he probably used that word undiscerningly on the regular five years ago. I was terrified to tell him I was gay (I consider myself bi, but felt like it would be easier to just tell him gay). Then he ended up being one of the first people I told, and since then has been nothing but supportive. Still, I didn’t necessarily expect him to talk about it with the guys at work, and hearing he did almost makes me teary eyed.
6 a.m. I had reheated pho for breakfast. Phenomenal choice.
10:30 a.m. I went on a three-mile run in the woods, and listened to My Dad Wrote a Porno. My best friend from college thinks it’s all a marketing stunt. I think it’s real. I think I’d like to get famous enough to get a drink with those guys, because they’re hilarious (and James could get it).
11:30 a.m. Log onto Grindr. Message a very cute guy I’ve never seen before. We chat a bit and he asked to see a shirtless picture. He then tells me to message him again when I lose some weight. Could you imagine saying that to someone?
Now, I’m in good shape, but look like I eat carbs now and then. You know that saying “Nothing tastes as good as skinny feels?” That’s bullshit. You know what tastes good? 6 a.m. pho.
6 p.m. I get dinner with a high-school friend I haven’t seen in a while. We eat shitty wings, drink shitty beer, and basically solve all the world’s problems. I’m bummed when we realize it’s past our bedtimes.
10:15 p.m. I run into Kayla, my sister’s best friend, having a smoke outside a bar near where I parked. She says I should come in for a drink. Bye bedtime!
12:15 AM: I hate myself for staying out so late, but ended up coming out to Kayla, which was really nice. We’re very close, but I hadn’t seen her in the right circumstances yet. I consider myself very lucky that my close friends and family do not give a shit.
11 a.m. I allow myself to sleep till now because 32-year-old hangovers are no joke. I do a quick jump rope workout and take an Uber downtown to get my car from where I left it the night before. I will 100 percent have a ticket, but also 100 percent have no DUI, so I guess it’s a wash.
12 p.m. Hanging out at my favorite coffee shop getting an almond tea latte, which sounds more pretentious than it is. I like this place because the baristas don’t treat you with disdain and their soundtrack is perennially yacht-rock (“You Can Call Me Al” never gets old). I’m pretending to read, but am actually Grinding it up.
12:15 p.m. Does sending a dick pic with no context ever work? Judging by his picture, this guy is a bartender at a place I semi-frequent. Now I’m going to feel awkward going there …
12:30 a.m. My sister was home tonight, so we had dinner and “just one more” Moscow Mule approximately four times at our favorite bar. We’re now in my parents’ basement drinking really bad wine and doing a deep dive on Game of Thrones Reddits. My sister lets me know that she has a secret account that she posts on, and that she’s gotten into some vicious Reddit arguments defending the Stark girls. I support this 100 percent.
10 a.m. Wake up feeling good, all things considered. I read a little, do some push-ups, and make myself a breakfast sandwich. I have nothing planned this weekend, and I’m excited to lay low. I have one of those aha moments where I delete all dating apps. This will last six days, but I’ll feel very holier than thou for at least the first three.
11 a.m. Not holier than thou enough to refrain from engaging in some good old fashioned cybersex via text with Tommy, a guy I met a couple years back at a music festival. He was one of the first hookups I ended up actually hanging out with afterward, and it’s a damn shame he lives in Texas. He always wants to do it on Snapchat, but the whole living-with-my-parents thing makes anything verbal difficult. Sigh.
1 p.m. My sister and I are back at the same bar we were at last night. Whoops.
3:30 p.m. We’re still here.
5 p.m. We’re no good for one another, but I’m staying hydrated.
7:30 p.m. Ending the week on a wholesome note. Office reruns in bed. No apps for me, at least not for another six days.
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